Sarah Nolan, a dedicated preschool teacher in her 40s and recently divorced, faces pressure from her family to reenter the dating world. Her sister, Carol, a relentless matchmaker, takes the initiative by crafting an online dating profile for Sarah on perfectmatch.com. This profile highlights her high school graduation photo and showcases her curvy figure, while also noting her fondness for dogs, particularly since she is currently caring for her brother Michael's Newfoundland amidst his marital challenges. However, Sarah's hopes of navigating dating smoothly are swiftly disrupted as she endures a series of ill-fated dates with a range of unsuitable candidates, including a weepy romantic, a rule-breaker, and others with dubious intentions.
In parallel, we meet Jake Anderson, another recent divorcee who is preoccupied with perfecting his boat designs rather than chasing after love. Despite Jake's disinterest, his friend Charlie believes he needs a push and sets him up with Sherry, a woman from their circle. Their initial meeting at an art gallery is painfully awkward, as Jake appears detached from trying to spark a connection. Charlie then introduces Jake to Sarah's profile and informs him about a date set for the following day at a local dog park.
When Sarah and Jake finally meet, the encounter is excruciatingly uncomfortable; Jake shows up with a borrowed terrier and starts critically examining Sarah's profile, only to admit that the dog isn’t his. When Sarah confronts him about the dishonesty, Jake cleverly notes that her profile stated "Must love dogs" rather than "Must own a dog," leading to an abrupt exit for Sarah, though she agrees to give him another shot.
As their relationship unfolds, Sarah and Jake share intimate dinners where they reveal their pasts. Sarah opens up about the painful aspects of her divorce, expressing her former husband’s disinterest in family life. She discovers that he has since moved on with a much younger partner who is now expecting a child. Their evening ends on a comedic note as the couple realizes they’ve forgotten to bring any condoms, resulting in a frantic and ultimately deflating quest around town to find them.
With autumn leaves dancing around them, Jake's curiosity about Sarah compels him to reach out that same night. Meanwhile, Sarah's budding connection with Bob Connor takes a turn when she arrives at his place only to find him cozying up with June, her co-worker. Hurt by this unexpected scenario, Sarah retreats, inadvertently leaving her wallet behind. Later, Jake is seen caring for Michael, creating a tender moment as he and Sarah share a kiss — this is soon interrupted by Bob's sudden appearance, who attempts to return her forgotten wallet and ends up sealing the moment with an unexpected kiss, which leaves Jake feeling disheartened.
Sarah's phone call to Bob becomes a defining moment, leading to a passionate night at a hotel, but the morning brings an unpleasant truth as she uncovers Bob's deceitful nature and his entanglement with June. Bob's reluctance to confess stems from his desire to keep their relationship alive, but his dishonesty ultimately proves overwhelming for Sarah.
As Jake navigates his own heartbreak, he finds himself constantly crossing paths with people who inadvertently guide him back to Sarah. A night out at the cinema with Sherry, featuring the classic film Doctor Zhivago, ignites Sarah’s feelings when she unexpectedly sees Jake on a date with Sherry. Her immediate departure from the scene echoes her earlier retreat from Bob’s advances.
Jake's encounter with Bill outside a coffee shop becomes crucial as Bill, unbeknownst to him, possesses insights about Sarah's true feelings. As Jake confides in Bill, receiving valuable advice, Sarah begins to decode her own emotions amidst the signs of destiny. In a climactic twist, a group of spirited girls from a local crew team orchestrates a rescue mission that brings Sarah and Jake together on the lake shores. Under a blanket of stars, they share a kiss that solidifies their profound connection — a bond forged through serendipity, fate, and their respective journeys through heartache.
